How to start sailing this summer

If there is a better way to experience the coast of Maine than sailing, I haven’t found it yet. Whether you are a local, a summer resident, or a visiting vacationer, you’ll never run out of harbors and islands to explore by boat.  Sailing silently and deliberately awakens each of your senses, and immerses you in the landscape. Gliding along in a light breeze you can hear the gulls, see the seals, feel the power of the wind and waves, smell the briny shores and taste the salt spray. It’s easy to understand the sentiment of longtime Maine resident E.B. White who wrote, “I cannot not sail.”


Sailing into Castine – Photo by M. Garand


Yet for those new to sailing the equipment, terminology, skills, and costs can be overwhelming. Fortunately, there are a variety of ways for everyone to go sailing that circumvent these barriers. Here are five ways to get started this summer:

1.) Community Boating

Community boating is a fantastic way to start sailing without spending a lot of money.  Many of these centers are operated as a nonprofit organization with the explicit goal of expanding access to boating for the local community. As a hub for sailing enthusiasts, community boating centers provide lessons, race coaching, summer camps, and after school programs. Most importantly, they provide direct access to boats. These programs benefit children and adults alike by fostering a passion for sailing at all levels. By starting with simple, small boats you will learn quickly. After a few basic lessons you’ll be able to rent or sign out boats to sail on you’re own. If you want to try sailing without the commitment of purchasing a boat, or the expense of a charter this is the way to go. These organizations are a great resource for the beginning sailor, particularly those with a limited budget.

2.) Sailing Classes

If you are looking for a more formal education in sailing, consider more specialized classes. Class topics range from basic sailing to offshore passage making. By attending a sailing school you will typically receive some form of certification. This is helpful if you are looking to charter a boat without a captain as the company will likely want to see that you have had some training. If you are considering buying a boat, but don’t have much experience, taking classes through a certified school may help reduce your insurance rate and will definitely improve your confidence. Classes range from a few hours to several days and are typically quite small. For a fee most schools will also offer private lessons if you are looking for more individual direction.

3.) Charters

There are many who love sailing, have some experience, but have no interest in owning or maintaining a boat. If this sounds like you, chartering a boat may be the perfect solution. What better way to enjoy a vacation than spending a week on a private boat? With a spectrum of boat sizes and styles available you’ll be able to fit the whole family or escape for a romantic getaway. Bareboat charters offer a well maintained boat for you to operate on your own in full privacy. If you don’t have the experience to take off on your own, consider a captained charter. Whether you want to learn under the careful watch of a seasoned sailor, or to cruise the coast without lifting a finger, there are options available. Charters can be a great way to expose the whole family to sailing without a long-term commitment. When they inevitably fall in love with it you may want to look into boat ownership, or some of the other opportunities on this list, as chartering is the most expensive way to enjoy sailing.

4.) Weekly Races

In addition to the community sailing programs previously mentioned, Maine is littered with yacht clubs and sailing communities. Many of these clubs host weekly evening races throughout the summer. While the competition can be stiff, many join for the social aspect and a cruise around the harbor. Racing a boat, especially a larger one, requires at least a few extra crew to trim, set, and strike sails. Owners looking for an extra hand will often post a flyer on local bulletin boards or online forums seeking crew. The more competitive skippers may require skilled crew, but many are happy to take on new sailors that are willing to listen and respond to commands. Immersing yourself in the world of racing can be a beneficial tool for understanding the concepts of sailing and an exciting way to meet a lot of other sailors. Networking among the community will lead to an endless supply of sailing opportunities as your skills progress.

5.) Traditional Sailing Vessels

With it’s rich maritime history and passion for the sea, Maine has always fostered a large fleet of sailing vessels. Once used for fishing and hauling cargo, many schooners and windjammers still sail as passenger vessels. Positions aboard can be hard to secure, particularly for the inexperienced, but opportunities do arise. Joining a traditional sailing vessel is a lifestyle of long hours, cramped quarters, and hard labor. In return you will enjoy full days on the water, beautiful sunsets and great food. If you can’t land a job on one of these historic boats, you may be able to volunteer in exchange for sailing opportunities. Keeping an old boat operating requires a lot of maintenance and many organizations rely heavily on volunteer support. As with the racing community, networking with ship owners and skippers will lead to more opportunities.

If you love the idea of sailing on an old windjammer, but don’t like the sound of hard labor, you should consider a vacation on one of these amazing vessels. Unlike a private charter you will be sharing the space with several other guests, a full crew and a chef. But for a taste of Maine’s rich sailing history, there is no better vacation. A variety of day sailing opportunities are available along the coast, with the majority of the extended cruises found in Penobscot Bay.

However you decide to do it, go sailing this summer. You won’t regret it. You don’t have to make it a full-time endeavor like I have, you don’t have to buy expensive gear, and you don’t have to already know how to sail. There is a path for you to the water.

A sampling of sailing opportunities in Maine:

Community Sailing:

Sail Maine – Portland

Rockland Community Sailing – Rockland

MDI Community Sailing Center – Southwest Harbor

St. George Community Sailing Center – Tenants Harbor

Come Boating – Belfast

Sailing Schools:

Morse Alpha Expeditions – Rockland

South Portland Sailing Center – South Portland

Sebago Sailing – South Casco

Old Quarry Sailing School – Stonington

Northeast Harbor Sailing School – Northeast Harbor

Boothbay Harbor Yacht Club Sailing School (open to non-members) – Boothbay Harbor


Bucks Harbor Charters – South Brooksville

North Point Yacht Charters – Rockport

Johanson Boatworks – Rockland

Hinckley Crewed Charters

Yacht North Group – North Yarmouth

Yacht Clubs:

There are numerous yacht clubs with summer programs, weekly races, and sailing schools. Check with you’re local club for available opportunities. Remember to check out the bulletin boards for “Crew Wanted” advertisements.

Traditional Sailing – Day Trips:

Maine Daysail – Belfast

Maine Sailing Adventures – Portland

Portland Schooner Company – Portland

Schooner Alert – Bailey Island

Schooner Eastwind – Boothbay Harbor

Schooner Olad – Camden

Traditional Sailing – Overnight Trips:

Maine Windjammer Cruises – Camden

Maine Windjammer Association

Schooner J. & E. Riggin – Rockland

The above list is by no means complete, but should help guide you on your search for a sailing adventure this summer. I do not have any affiliation with the aforementioned companies.

Matt Garand

About Matt Garand

Lifelong Mainer, and professional mariner, Matt Garand is the creator of A Life Aboard, a look at year-round living on a sailboat in Maine. Matt and his wife, Skye, live aboard in South Portland and use every available chance to throw off the lines and explore the coast.